So I got in touch with an old friend from my teen years that I used to play D&D 3.5 with. I learned though that they have not GM'd a game since because of poor interpretation of rules and Chaotic Random characters, it was a hot mess. I feel partially to blame, but we're planning to get together and give it another shot, as I have now GM'd so many games that I know how to curb those types of behaviors (and not instigate them).
With this in mind, we want to keep it simple. What recommendations would you have for a pre-made module that could be played with just 1 player (possibly multiple characters as there are very few 1 PC adventures), that are good for a beginner GM?
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I suggest Master of The Fallen Fortress to start. It's short, but it has a good variety of encounters. Then maybe the First Steps series. All of these are free.
Maybe you can find a PFS (organized play) group in your area.
Look HERE.